Diarylmethylene disulfide compound as well as preparation method and application thereof
A technology for compounds and preparations, applied in the field of diarylmethylene disulfide compounds and their preparation, can solve the problems of limited treatment means and great harm of cerebral apoplexy, etc.
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Embodiment 1
[0055] Example 1 1,2-bis[(3,5,6-trimethylpyrazin-2-yl)methyl]disulfide (LYY-Ι 1 )
[0056] 1-bromotetramethylpyrazine (0.210g, 0.97mmol), thiourea (0.111g, 1.45mmol), sodium carbonate (0.154g, 1.45mmol), manganese dioxide (0.084g, 0.97mmol) were added to a 100mL reaction flask , then add wet-PEG200 (20mL) (PEG200:H 2 O=10:1), heated to 40°C, and stirred for 3h. Cool to room temperature, add water (20mL), extract with ethyl acetate (20mL) three times, wash with water (50mL) three times, dry over anhydrous magnesium sulfate, filter with suction, column chromatography [eluent petroleum ether: ethyl acetate (v :v)=10:1], a yellow solid was obtained. Yield 45%. Mp: 73~75℃.
[0057] 1 H NMR (400MHz, CDCl 3 ), δ (ppm): 3.99 (s, 4H, CH 2 ),2.54(s,6H,CH 3 ),2.49(s,12H,CH 3 ).
[0058] 13 C-NMR (600MHz, CDCl 3 ), δ(ppm): 150.17, 148.94, 148.64, 146.61, 42.67, 21.62, 21.40, 21.09.
[0059] HR-MS:[M+H] + , Calcd: 335.1364, Found: 335.1360.
Embodiment 2
[0060] Example 2 1,2-dibenzyl disulfide (LYY-Ι 2 )
[0061] Reference compound LYY-Ι 1 The synthesis method is prepared from benzyl bromide and thiourea to obtain a white solid. Yield 57%. Mp: 64~68℃.
[0062] 1 H NMR (400MHz, CDCl 3 ,δ(ppm):7.35-7.32(m,2H,ArH),7.32-7.28(m,4H,ArH),7.24(dd,J=5.8,4.3Hz,4H,ArH),3.60(s,4H, CH 2 ).
[0063] 13 C-NMR (600MHz, CDCl 3 ), δ(ppm): 137.60, 129.65, 128.72, 127.66, 43.03.
[0064] HR-MS:[M+H] + , Calcd: 247.0615, Found: 247.0611.
Embodiment 3
[0065] Example 3 4,4'-Disulfanediyl bis(methylene)dibenzoate methyl ester (LYY-I 3 )
[0066] Reference compound LYY-Ι 1 The synthesis method is prepared from 4-(bromomethyl)methyl benzoate and thiourea to obtain a white solid. Yield 51%. Mp: 81~85℃.
[0067] 1H NMR (400MHz, CDCl 3 ), δ (ppm): 8.01–7.97 (m, 4H, ArH), 7.28 (d, J = 8.3Hz, 4H, ArH), 3.92 (s, 6H, OCH 3 ),3.62(s,4H,CH 2 ).
[0068] 13C-NMR (600MHz, CDCl 3 ), δ(ppm): 166.80, 142.61, 129.86, 129.41, 129.35, 52.21, 42.91.
[0069] HR-MS:[M+H] + , Calcd: 363.0725, Found: 363.0724.
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